I am planning on a bareboat charter in December somewhere in the Grenadines but am struggling to find flights under $1000 pp from PHL. Does anyone have recommendations for websites or travel agents who have expertise in this region? Or do I just suck it up?!

That is a long trip. I would not expect prices to be low. Flew from Maine to st. Vincent in 2010 and it was at least $1000 ea.

Flying direct Boston to st. Thomas next year for a bvi charter. Flight was about $1000 for two of us. Then we take the ferry.

Direct flights will cost more. Try flights with more stops.

Chartering in the Grenedines is fun. It not for the first time charterer. Strong tr winds will sail you down the chain fine but tacking back against unfavorable winds and currents including some decent wave height is not fun for any non sailors.

You have to be creative with this.
Fly out of Atlantic City on Spirit. That can get you to San Juan, St Thomas or St Martin. Its Spirit.com
Once you're on island you can do Liat, American Eagle or charter from St Martin to your final destination. I did a quick search from ACY to SJU and it was $206 each way.
Good Luck and enjoy!

Thanks
Figured out that Miami and Barbados are hubs and went from there.
The ACY flights to the Leewards looked interesting but unfortunately aren't so cheap when you book in December. Thanks for heads up on Spirit though!

Interesting suggestions. Thanks!
We have 10 or so days, at the end of december. I had been thinking about pottering round the south of Grenada for a few days, leaving from St Davids then shooting up to Carriacou/Mayreau/Cays then returning to Grenada. It's not my preference to go up the East side of Grenada, so shout if you think that's insane, even for passage making to get to the center of things.
I chartered a few years ago out of St Vincent, got no further than PSV and returned. Just a 7 day cruise. Fantastic trip, great weather but big swells from NNE. The journey north was horrible! Especially the last morning from Port Elizabeth to St V. Quite happy to leave the northern end of the chain well alone...
In any case, just planning is fun

I think for Grenada, our flight options are narrow if we wanted to go direct. Either out of Miami or JFK. Kayak.com and Priceline seemed to give the best options, but one route suggested NYC via London Gatwick to Grenada! The most suitable departs PHL and is $890 rtn. Not so bad for holiday time.
It's clear that the airlines have stripped capacity over the last few years because of the economic climate. I feel for the islands given the impact this must have on their tourist trade.

The best kept secret in puddle jumping airlines is they don't actually lose your luggage. The weight and balance limitations of those aircraft often will not allow them to fill every seat and bring luggage for every passenger. They know they are leaving it behind, the moment you give it to them. If it goes elsewhere, it's often logistics of how to connect it to you, rather than sit at your departure terminal. If you can, pack light and carry on.

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